Kieran, a Republic of Ireland youth international, was a part of West Ham's youth academy before moving to St. Mirren in January 2015. He went on to make eleven league appearances for the club, scoring once in a 4-1 win over Kilmarnock, as the club finished bottom of the Scottish Premiership. He left the club at the end of his contract in June and moved to Peterborough United, under manager Dave Robertson, in July 2015 after a successful trial.

Kieran made his Peterborough debut, and his only senior appearance for the club, in the 4-1 loss to Charlton Athletic in the League Cup. He joined Halifax Town on loan in October, making eight league appearances before returning to Peterborough in January 2016. Soon after this Kieran signed for Sligo Rovers, now managed by his former Peterborough boss, Dave Robertson.

Kieran made his debut for Sligo Rovers on the opening weekend of the 2016 season against Shamrock Rovers and scored his first goals against Galway United in May, scoring both Sligo goals in a 2-1 win. Kieran made 28 league appearances that year, scoring eight times, as Sligo finished fifth in the Premier Division.

Kieran signed for Cork City in the summer of 2017 and was part of the side to win the league and FAI Cup double that season. Sadlier scored five goals as well as the winning penalty in the cup final shootout.
Following the conclusion of the 2018 season, Kieran returned to England and signed for League One side Doncaster Rovers.

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